Hollister
An older non-gated Windermere pocket with mature oaks and custom estates.
Live the MaxLife.
$1.1M
Median Price
$700K – $1.8M
130
Homes
$0–$60
Monthly HOA
1985
Established
Windermere Elementary
School Zone
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Background
A brief history
Hollister was platted in the mid-1980s on land that had been part of the original Windermere citrus holdings — one of the older non-gated residential areas that predates the gated-community wave of the 1990s and 2000s. Roughly 130 custom lots were released, most built out between 1985 and 2000 as one-off customs. The neighborhood's light governance (minimal HOA, no architectural review on most lots) is the reason Hollister reads as architecturally varied today — 1980s two-story colonials, 1990s ranches, 2000s Mediterraneans, and a growing share of 2018+ farmhouse rebuilds share the same streets.
The feel
What it's like to live here
Hollister has the feel of an established Windermere neighborhood rather than a curated community — the kind of place where neighbors have lived for 20+ years and the tree canopy has grown in enough that summer afternoons stay cool under shade. Streets are lightly-trafficked two-lanes with no gate, no sidewalks on some blocks, and mature live-oak canopy throughout. Lots run 0.3 to 0.6 acre. The mix of long-tenured residents and newer renovation buyers gives the neighborhood a settled-but-refreshing character. Daily life orients around Windermere downtown (5 minutes) and the 429 for commute access.
The details
What to expect
Architecture & Lots
Architecturally mixed across four decades — 1980s two-story colonials, 1990s ranches, 2000s Mediterraneans, 2018+ farmhouse rebuilds. Main homes 2,600–4,800 square feet. Lots 0.3 to 0.6 acre. Mature live-oak canopy throughout.
Lifestyle & Amenities
Non-gated, no community pool or clubhouse. The tree canopy and neighborhood quiet are the amenities. Residents walk or bike to Windermere downtown, Fort Gatlin Park, and the chain of city parks. Weekend farmers' market in downtown Windermere is a local institution.
HOA Rules & Fees
Annual HOA $0–$720 (some blocks have small HOAs for road and common-area maintenance; others have none at all). No architectural review. Short-term rentals technically permitted but uncommon. Low-restriction neighborhood — one of the reasons buyers choose Hollister over a gated community.
Schools
Schools named for the area: Windermere Elementary, Gotha Middle, and Olympia High. Assignment follows the street address, so check each home in OCPS Find My School before you write an offer. Windermere Prep (private) is 4 minutes.
Access & Commute
Four minutes to Windermere downtown, 10 minutes to the 429, 15 minutes to Disney, 20 minutes to Restaurant Row, 30 minutes to MCO.
Community
Amenities
- Mature live-oak canopy throughout
- Four minutes to Windermere downtown
- Non-gated with minimal HOA governance
- Architecturally varied custom-build stock
- Lower entry point for Windermere
Know Before You Buy
HOA rules worth knowing
- Annual HOA $0–$720 depending on block
- No architectural review
- Short-term rentals permitted but uncommon
- Non-gated community
Education
School assignments
- Windermere Elementary
- Gotha Middle School
- Olympia High School
- Windermere Prep (private)
School zone assignments change. Verify with the Orange County school district before purchase.
Market Commentary
What the market is doing
Current median trades in the $1M–$1.2M band. Unrenovated 1980s–1990s originals move $700K–$950K. Well-renovated homes run $1.1M–$1.5M. Recent custom rebuilds have closed $1.6M–$1.8M. Price-per-square-foot runs $250 for dated originals to $340 for renovated. Renovation status and lot size are the primary value drivers. Days-on-market has averaged 35–60 days.
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Homes near Hollister
Nothing is listed in Hollister right now. Showing homes in Windermere. Many Hollister homes sell off-market — get notified first when new inventory comes available.
$1,845,000
4282 Mckinnon Rd
Windermere, FL 34786
6 bd · 6 ba · 5,869 sqft
Windermere
MLS ID #O6432910, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$297,997
8168 Boat Hook Loop #302
Windermere, FL 34786
2 bd · 2 ba · 1,161 sqft
Lakeside/Lks/Windermere
MLS ID #O6445290, BLUE KEY PROPERTY MANAGEMENT.
Listing provided by Stellar MLS
$630,000
8582 Powder Ridge Trl
Windermere, FL 34786
4 bd · 4 ba · 2,454 sqft
Windermere Trls Ph 3b
MLS ID #S5158690, LPT REALTY, LLC.
Listing provided by Stellar MLS
$1,999,000
713 Main St
Windermere, FL 34786
6 bd · 6 ba · 5,031 sqft
Windermere
MLS ID #O6368185, THE REAL ESTATE COLLECTION LLC.
Listing provided by Stellar MLS
$1,799,000
7413 Lake Albert Dr
Windermere, FL 34786
6 bd · 7 ba · 4,945 sqft
Lake Burden South Ph I
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6451030, GOLFPARK PROPERTIES.
Listing provided by Stellar MLS
$562,000
7271 Londale Blvd
Windermere, FL 34786
3 bd · 2 ba · 1,855 sqft
Enclave/Berkshire Park B G H I
MLS ID #O6445539, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 25, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA